Composition for enhancing immunity containing amide-based compound

Abstract

The present specification relates to a composition containing a novel amide-based compound derived from an amino acid structure such as valine, leucine, phenylalanine, proline, or pipecolic acid, and the composition can exhibit an immune-enhancing effect by activating the phagocytosis of macrophages, which aids in removing pathogenic bacteria as an important part of the human immune system.

We claim: 
     
         1 . A method for enhancing immunity, the method comprising administering an effective amount of a composition containing, as an active ingredient, a compound represented by the following Chemical Formula 1, a stereoisomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof to a subject in need thereof: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 1, 
         X is represented by any one of the following Chemical Formulae 1-1 to 1-5, 
       
       
         
           
           
               
               
           
         
         in Chemical Formula 1-1, 
         Ar is phenyl unsubstituted or substituted with one to three R 1 , 
         R 1  is hydrogen, a phenyl group, a C1-C4 alkoxy group, a C1-C4 alkyl group, a fluoro group, an adamantane group, an acetylamino group, or a hydroxyiminoethyl group, 
         when there are more than one R 1  residue, all R 1  residues are the same as each other, 
         in Chemical Formula 1-2, 
         Ar is phenyl substituted with one R 2 , 
         R 2  is a C1-C4 alkyl group, a C1-C4 alkoxy group, an adamantane group, an acetyl group, or an acetylamino group, 
         in Chemical Formula 1-3, 
         Ar is phenyl substituted with one to three R 3  or unsubstituted naphthalene, 
         R 3  is hydrogen, or a C1-C4 alkyl group or a phenyl group, 
         when there are more than one R 3  residue, all R 3  residues are the same as each other, 
         in Chemical Formula 1-4, 
         Ar is phenyl unsubstituted or substituted with one to three R 4 , 
         R 4  is hydrogen, a phenyl group, a C1-C4 alkyl group, or a C1-C4 alkoxy group, 
         when there are more than one R 4  residue, all R 4  residues are the same as each other, 
         in Chemical Formula 1-5, 
         Ar is phenyl substituted with one to three R 5 , 
         R 5  is a C1-C4 alkyl group or a phenyl group, and 
         when there are more than one R 5  residue, all R 5  residues are the same as each other. 
       
     
     
         2 . The method of  claim 1 , wherein the compound represented by Chemical Formula 1 is any one selected from the following compounds:
 N-hydroxy-1-(phenylsulfonyl) piperidine-2-carboxamide,   1-([1, l′-biphenyl]-4-ylsulfonyl)-N-hydroxypiperidine-2-carboxamide,   1-((4-(tert-butyl)phenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   1-((4-butoxyphenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   N-hydroxy-1-(mesitylsulfonyl) piperidine-2-carboxamide,   2-([1,1′-biphenyl]-4-sulfonamido)-N-hydroxy-3-phenylpropanamide,   2-((4-(tert-butyl)phenyl) sulfonamido)-N-hydroxy-3-phenylpropanamide,   N-hydroxy-3-phenyl-2-((2,4,6-trimethylphenyl) sulfonamido) propanamide,   N-hydroxy-2-(naphthalene-2-sulfonamido)-3-phenylpropanamide,   2-([1,1′-biphenyl]-4-sulfonamido)-N-hydroxy-4-methylpentanamide,   2-((4-(tert-butyl)phenyl) sulfonamido)-N-hydroxy-4-methylpentanamide,   2-((4-butoxyphenyl) sulfonamido)-N-hydroxy-4-methylpentanamide,   N-hydroxy-4-methyl-2-((2,4,6-trimethylphenyl) sulfonamido) pentanamide,   2-([1,1′-biphenyl]-4-sulfonamido)-N-hydroxy-3-methylbutanamide,   2-((4-(tert-butyl)phenyl) sulfonamido)-N-hydroxy-3-methylbutanamide,   N-hydroxy-3-methyl-2-((2,4,6-trimethylphenyl) sulfonamido) butanamide,   1-((4-fluorophenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   1-((4-((3r,5r,7r)-adamantan-1-yl)phenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   N-hydroxy-1-((4-propylphenyl) sulfonyl) piperidine-2-carboxamide,   1-((4-acetamidophenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   1-((4-(tert-butyl)phenyl) sulfonyl)-N-hydroxypyrrolidine-2-carboxamide,   1-((4-butoxyphenyl) sulfonyl)-N-hydroxypyrrolidine-2-carboxamide,   1-((4-((3r,5r, 7r)-adamantan-1-yl)phenyl) sulfonyl)-N-hydroxypyrrolidine-2-carboxamide,   N-hydroxy-1-((4-propylphenyl) sulfonyl) pyrrolidine-2-carboxamide,   1-((4-acetylphenyl) sulfonyl)-N-hydroxypyrrolidine-2-carboxamide,   N-hydroxy-1-((4-(1-(hydroxyimino)ethyl)phenyl) sulfonyl) piperidine-2-carboxamide,   N-hydroxy-4-methyl-2-(phenylsulfonamido) pentanamide, and   1-((4-acetamidophenyl) sulfonyl)-N-hydroxypyrrolidine-2-carboxamide.   
     
     
         3 . The method of  claim 1 , wherein the compound represented by Chemical Formula 1 is any one selected from the following compounds:
 N-hydroxy-1-(phenylsulfonyl) piperidine-2-carboxamide,   1-([1,1′-biphenyl]-4-ylsulfonyl)-N-hydroxypiperidine-2-carboxamide,   1-((4-(tert-butyl)phenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   2-([1,1′-biphenyl]-4-sulfonamido)-N-hydroxy-3-phenylpropanamide,   2-((4-(tert-butyl)phenyl) sulfonamido)-N-hydroxy-4-methylpentanamide,   2-((4-butoxyphenyl) sulfonamido)-N-hydroxy-4-methylpentanamide,   N-hydroxy-4-methyl-2-((2,4,6-trimethylphenyl) sulfonamido) pentanamide,   2-([1,1′-biphenyl]-4-sulfonamido)-N-hydroxy-3-methylbutanamide,   1-((4-((3r,5r,7r)-adamantan-1-yl)phenyl) sulfonyl)-N-hydroxypiperidine-2-carboxamide,   1-((4-butoxyphenyl) sulfonyl)-N-hydroxypyrrolidine-2-carboxamide, and   N-hydroxy-1-((4-propylphenyl) sulfonyl) pyrrolidine-2-carboxamide.   
     
     
         4 . The method of  claim 1 , wherein the compound represented by Chemical Formula 1 is derived from an amino acid. 
     
     
         5 . The method of  claim 1 , wherein the enhancing immunity is activating a phagocytosis of macrophages. 
     
     
         6 . The method of  claim 1 , wherein the enhancing immunity is activating a phagocytosis of macrophages against  S. aureus.    
     
     
         7 . The method of  claim 1 , wherein the enhancing immunity is strengthening the skin barrier. 
     
     
         8 . The method of  claim 1 , wherein the enhancing immunity is suppressing skin inflammation. 
     
     
         9 . The method of  claim 1 , wherein the composition is a cosmetic composition. 
     
     
         10 . The method of  claim 1 , wherein the composition is a skin external preparation. 
     
     
         11 . The method of  claim 1 , wherein the composition is a food composition. 
     
     
         12 . The method of  claim 1 , wherein the composition is a pharmaceutical composition. 
     
     
         13 . The method of  claim 12 , wherein the enhancing immunity is preventing, ameliorating, or treating skin inflammation. 
     
     
         14 . The method of  claim 1 , wherein a content of the active ingredient is 0.01 μM to 100 mM based on a total volume of the composition. 
     
     
         15 . The method of  claim 1 , wherein a daily application amount of the active ingredient is 1 to 1,000 mg/kg. 
     
     
         16 . The method of  claim 1 , wherein cells are treated with the active ingredient at a concentration of 1 to 100 μM.